Silver acetate

• CAS: 563-63-3
• Catalog Number: ACM563633
• Category: Main Products
• Molecular Weight: 166.91
• Molecular Formula: C2H3AgO2
• Description: Silver acetate is an inorganic compound with the empirical formula CH3CO2Ag (or AgC2H3O2). It is a photosensitive, white, crystalline solid. It is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion. It has been used in some antismoking drugs.
• Synonyms: Acetic acid silver(I) salt
• IUPAC Name: Silver;acetate
• Canonical SMILES: CC(=O)[O-].[Ag+]
• InChI: InChI=1S/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
• InChI Key: CQLFBEKRDQMJLZ-UHFFFAOYSA-M
• Melting Point: 2000ºC
• Flash Point: 40ºC
• Density: 3.259 g/cm³
• Solubility: Soluble in 100 parts cold water
• Appearance: White to gray solid
• Application: 3 - 1 - Carbonylation Silver acetate, when combined with carbon monoxide (CO), can induce the carbonylation of primary and secondary amines. Other silver salts can be used but the acetate gives the best yield. 2 R2NH + 2 AgOAc + CO → [R2N]2CO + 2 HOAc + 2 Ag 3 - 2 - Hydrogenation Silver acetate in a solution of pyridine absorbs hydrogen and is reduced to metallic silver. 3 - 3 - Direct ortho - arylation Silver acetate is a useful reagent for direct ortho-arylation (to install two adjacent substituents on an aromatic ring) for of benzylamines and N-methylbenzylamines. The reaction is palladiumcatalized and requires a slight excess of silver acetate.This reaction is shorter than previous ortho-arylation methods.
• Storage: Store below +30 °C
• Complexity: 25.5
• Covalently-Bonded Unit Count: 2
• Defined Atom Stereocenter Count: 0
• EC Number: 209-254-9
• Exact Mass: 165.9184
• Formal Charge: 0
• Hazard Codes: Xi
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Heavy Atom Count: 5
• HS Code: 28432900
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 0
• LogP: 0.01380
• Monoisotopic Mass: 165.9184
• PSA: 26.3
• RIDADR: UN 1759
• Rotatable Bond Count: 0
• Stability: Stability Stable, but light sensitive. Incompatible with strong reducing agents.
• Storage Conditions: Do not store in direct sunlight. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
• Topological Polar Surface Area: 40.1 Ų
• UNII: 19PPS85F9H
• WGK Germany: 3

Case Study

Synthesis of Silver Acetate in Nanoparticle Preparation and Hydrogen Peroxide Decomposition

Abu-Zied B. M, et al. Thermochimica Acta, 2014, 581, 110-117.

The approach involves heating silver acetate (AgAc) in air or nitrogen atmospheres, where it decomposes to form metallic silver (Ag) nanoparticles (NPs), along with minor amounts of silver oxide (Ag2O) and carbon-containing substances. The thermal behavior of AgAc, as analyzed through thermogravimetric analysis (TGA) and differential thermal analysis (DTA), shows that complete decomposition occurs between 150°C and 600°C, with silver metal being the primary product. This process yields silver nanoparticles with a particle size ranging from 10 to 35 nm, as confirmed by Transmission Electron Microscopy (TEM).
The synthesized silver nanoparticles, denoted as Ag-x (where x represents the calcination temperature), exhibit significant catalytic activity, particularly in the decomposition of hydrogen peroxide (H2O2) at temperatures between 35°C and 50°C. These properties make silver nanoparticles an ideal catalyst for various oxidation reactions, showcasing their functional role in chemical processes.

Silver Acetate in Aminolysis Reactions: A Key Reagent for Benzoylation

Leggio A, et al. Tetrahedron Letters, 2015, 56(1), 199-202.

Silver acetate (AgAc) serves as a crucial reagent in the aminolysis of acyl chlorides, particularly in the benzoylation of amino groups. In a study using benzoyl chloride and N,N-diethylamine, silver acetate facilitated the reaction in diethyl ether at room temperature, completing in just 15 minutes. The reaction efficiency was highly dependent on the experimental conditions, with optimal results achieved by using a stoichiometric amount of silver acetate and sodium acetate. Under these conditions, the reaction proceeded smoothly, producing N,N-diethylbenzamide in an 87% yield, while avoiding undesired side reactions such as the reduction of silver ions when protected from light.
Further optimization indicated that the sequence of reagent addition played a pivotal role in the outcome. When the acyl chloride and silver acetate were mixed first, a mixed anhydride formed, leading to a mixture of products. However, adding silver acetate after the amine led to selective benzoylation, highlighting the importance of reaction sequence in determining the final product.

Silver Acetate in the Groebke-Blackburn-Bienayme Reaction for Sustainable Synthesis of Imidazo[1,2-a]pyridines

Hussain M, et al. Journal of Heterocyclic Chemistry, 2020, 57(3), 955-964.

Silver acetate (AgOAc) plays a pivotal role in the silver-catalyzed Groebke-Blackburn-Bienayme (GBB) reaction, enabling the efficient synthesis of 3-aminoimidazo-fused heterocycles. In this sustainable approach, ethylene glycol is used as a biodegradable solvent, further enhancing the environmental friendliness of the process. The reaction involves the coupling of isocyanides, various aryl aldehydes, and an amino heterocycle, facilitated by AgOAc as the catalyst. The one-pot reaction proceeds with excellent yields and high atomic economy, offering an eco-friendly alternative to traditional methods that typically rely on toxic solvents.

Custom Q&A

What is the chemical formula of silver acetate?

The chemical formula of silver acetate is CH3COOAg.

What is the molecular weight of silver acetate?

The molecular weight of silver acetate is 166.91.

What is the color of silver acetate?

Silver acetate is white to gray in color.

What is the melting point of silver acetate?

Silver acetate decomposes at its melting point.

What are some synonyms of silver acetate?

Some synonyms of silver acetate are silver acetate purum p.a., acetic acid, silver acetate 99.99% trace metals basis, and silver acetate anhydrous.

How is silver acetate used in the laboratory?

Silver acetate is used as a reagent for direct ortho-arylation, conversion of organohalogen compounds into alcohols, and as a catalyst in cycloaddition reactions.

What is the solubility of silver acetate?

Silver acetate has a solubility of 10.2g/L.

How is silver acetate synthesized?

Silver acetate can be synthesized by the reaction of acetic acid and silver carbonate or by treatment of silver nitrate with sodium acetate.

What are some reactivity profiles of silver acetate?

Silver acetate is freely soluble in dilute nitric acid and can serve as an oxidizing agent.

How is silver acetate used as a deterrent for smoking?

Silver acetate is used in gum, spray, and lozenges to deter smokers from smoking by creating an unpleasant metallic taste in the smoker's mouth when mixed with smoke.